Cyclohexanol → HCID 14771304, compound

HRID 476733Notes

Reaction equation

HRID 476733 reaction equation
[H-].[Na+].[CH:3]1([OH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18]>O1CCOCC1>[CH:3]1([O:9][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N+:17]([O-:19])=[O:18])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 14771304HCID 14771304, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To 40 ml of a dioxane suspension containing 0.92 g of 60% sodium hydride was added 2.5 ml of cyclohexanol at room temperature over a 15-minute period, and the mixture was stirred at the same temperature for 1 hour and then at 50° C. for 3.5 hours. The temperature of the reaction solution was returned to room temperature, 10 ml of a dioxane containing 3.2 g of 2-fluoronitrobenzene was added dropwise, and the mixture was stirred at room temperature overnight. The dioxane was evaporated, the residue was extracted with chloroform, and the chloroform layer was washed, in turn, with water and a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was evaporated to give an oil, which was then distilled under reduced pressure to give 3.8 g of 2-cyclohexyloxynitrobenzene.

Workup

  1. waitat 50° C. for 3.5 hours
  2. customwas returned to room temperature
  3. stirringthe mixture was stirred at room temperature overnight
  4. customThe dioxane was evaporated
  5. extractionthe residue was extracted with chloroform
  6. washthe chloroform layer was washed, in turn, with water
  7. dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customto give an oil, which
  10. distillationwas then distilled under reduced pressure

Sources & evidence

ORD record
ord-86d185b0bfc440bdb9d5e1661b7cb626
Source dataset
uspto-grants-1989_12
Patent number
US04885367

Reaction notes

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